title: Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.
abstract: Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University.
authors.forename: Kiyofumi
authors.initials: K
authors.lastname: Inamoto
mesh_terms: D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D052160:Benzothiazoles; D006571:Heterocyclic Compounds; D007191:Indazoles; D007211:Indoles; D015363:Quinolones; D013876:Thiophenes; C088015:benzothiophene; D010165:Palladium; D002244:Carbon; D006859:Hydrogen